1000623-98-2

Basic information

• Product Name: 2,5-Di(HD)-3,6-di(5-broMothiophen)diketopyrrolopyrrole
• Synonyms: 2,5-Di(HD)-3,6-di(5-broMothiophen)diketopyrrolopyrrole;3,6-Bis(5-broMo-2-thienyl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione;3,6-bis(5-broMo-2-thienyl)-2,5-bis(2-hexyldecyl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione DPP-iC16;Pyrrolo[3,4-c]pyrrole-1,4-dione,3,6-bis(5-bromo-2-thienyl)-2-5-bis(2-hexyldecyl)-2,5-dihydro-;3,6-bis(5-bromothiophen-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione;3,6-Bis(5-bromo-2-thienyl)-2,5-bis(2-hexyldecyl)-2,5-dihydro-pyrrolo[3,4-c]pyrrole-1,4-dione 98%
• CAS NO: 1000623-98-2
• Molecular Formula: C₄₆H₇₀Br₂N₂O₂S₂
• Molecular Weight: 906.9982
• EINECS: -0
• Mol File: 1000623-98-2.mol
• Article Data: 7

Chemical Properties

• Melting Point: 110-115°C
• Boiling Point: 865.4±65.0 °C(Predicted)
• Appearance: /
• Density: 1.24±0.1 g/cm3(Predicted)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: -5.29±0.60(Predicted)
• CAS DataBase Reference: 2,5-Di(HD)-3,6-di(5-broMothiophen)diketopyrrolopyrrole(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Di(HD)-3,6-di(5-broMothiophen)diketopyrrolopyrrole(1000623-98-2)
• EPA Substance Registry System: 2,5-Di(HD)-3,6-di(5-broMothiophen)diketopyrrolopyrrole(1000623-98-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 1000623-98-2(Hazardous Substances Data)

Usage

Description

3,6-bis(5-bromothiophen-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione (DPP-HD-2ThBr) is a family member of?pyrrolopyrrole-dione (DPP). This monomer has been used for the synthesis of?PDPP3T, which is a low band-gap polymer semiconductor?commonly used?as i) a polymer donor material for OPV, and ii) hole-transport layer (HTL) for perovskite solar cells.

Uses

DDP-Br2 can be used in the fabrication of a variety of opto-electronic devices such as organic field effect transistors (OFETs), perovskite based solar cells, non-fullerene organic solar cells.

General Description

3,6-Bis(5-bromo-2-thienyl)-2,5-bis(2-hexyldecyl)-2,5-dihydro-pyrrolo[3,4-c]pyrrole-1,4-dione (DDP-Br2) belongs to the series of diketopyrrolopyrrole (DPP) based materials which show hole or ambipolar transport behavior with mobilities of charge carriers in the range of 0.1-1 cm2V-1 s-1. It has an electron deficient core that forms a low LUMO energy level which facilitates better air-stability for n-type organic semiconductors.

Synthetic route

3,6-bis(5-bromothien-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione (1044598-80-2) → 3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione (1000623-98-2)

Conditions	Yield
With N-Bromosuccinimide In chloroform at 50℃; for 2h; Inert atmosphere;	79.9%
With N-Bromosuccinimide In chloroform for 48h; Darkness;	61%
With N-Bromosuccinimide In chloroform for 48h; Darkness;	60%

3,6-bis(5-bromothien-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione (1044598-80-2) → 3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione (1000623-98-2) + 3-(5-bromothiophen-2-yl)-2,5-bis(2-hexyldecyl)-6-(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione (1423138-95-7)

Conditions	Yield
With N-Bromosuccinimide In chloroform at 0 - 20℃; Darkness;	A 17% B 56%

3,6-dithiophen-2-yl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione + 7-(iodomethyl)pentadecane (1044598-79-9) → 3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione (1000623-98-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 120 °C 2: N-Bromosuccinimide / chloroform / 20 °C View Scheme

thiophene-2-carbonitrile (1003-31-2) → 3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione (1000623-98-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium / tert-Amyl alcohol / 120 °C 2: potassium carbonate / N,N-dimethyl-formamide / 120 °C 3: N-Bromosuccinimide / chloroform / 20 °C View Scheme
Multi-step reaction with 3 steps 1: potassium tert-butylate / tert-Amyl alcohol / 4 h / 110 °C 2: potassium carbonate / N,N-dimethyl-formamide / 24 h / 110 °C 3: N-Bromosuccinimide / chloroform / 48 h / Darkness View Scheme
Multi-step reaction with 3 steps 1.1: potassium tert-butylate / tert-Amyl alcohol / 5 h / 110 °C / Inert atmosphere 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 130 °C / Inert atmosphere 2.2: 130 °C / Inert atmosphere 3.1: N-Bromosuccinimide / chloroform / 2 h / 50 °C / Inert atmosphere View Scheme

2-hexyldecan-1-ol (2425-77-6) → 3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione (1000623-98-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 20 °C 2: potassium carbonate / N,N-dimethyl-formamide / 120 °C 3: N-Bromosuccinimide / chloroform / 20 °C View Scheme

3,6-dithiophen-2-yl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione → 3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione (1000623-98-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 24 h / 110 °C 2: N-Bromosuccinimide / chloroform / 48 h / Darkness View Scheme

3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione (1000623-98-2) + 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole (24388-23-6) → 2,5-bis(2-hexyldecyl)-3,6-bis(5-phenylthiophen-2-yl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione

Conditions

Yield

Stage #1: 3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione; 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole With tris-(dibenzylideneacetone)dipalladium(0); Aliquat (at)366; triphenylphosphine In water; toluene for 0.25h; Schlenk technique; Inert atmosphere; Stage #2: With potassium phosphate In water; toluene at 115℃; for 16h; Schlenk technique; Inert atmosphere; Sealed tube;

97%

3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione (1000623-98-2) + 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole (24388-23-6) → 2,5-bis(2-hexyldecyl)-3,6-bis(5-phenylthiophen-2-yl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione + C104H150N4O4S4

Conditions

Yield

Stage #1: 3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione; 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole With tris-(dibenzylideneacetone)dipalladium(0); Aliquat (at)366; triphenylphosphine In water; toluene Schlenk technique; Inert atmosphere; Stage #2: With potassium phosphate In water; toluene at 115℃; Schlenk technique; Inert atmosphere; Sealed tube;

A 87% B 6.6%

3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione (1000623-98-2) + 2-Ethynylanthracene (78053-56-2) → 3,6-bis(5-(anthracen-2-ylethynyl)thiophen-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); N-ethyl-N,N-diisopropylamine In toluene at 60℃; for 8h; Sonogashira Cross-Coupling; Inert atmosphere; Schlenk technique;	75%

3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione (1000623-98-2) + C15H15BF2N2 (1625689-09-9) → C76H98B2F4N6O2S2

Conditions	Yield
Stage #1: 3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); N-ethyl-N,N-diisopropylamine In tetrahydrofuran Schlenk technique; Inert atmosphere; Stage #2: C15H15BF2N2 In tetrahydrofuran at 60℃; for 3h; Inert atmosphere;	75%

3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione (1000623-98-2) + phenylacetylene (536-74-3) → 2,5-bis(2-hexyldecyl)-3,6-bis(5-(phenylethynyl)thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); N-ethyl-N,N-diisopropylamine In toluene at 60℃; for 8h; Sonogashira Cross-Coupling; Inert atmosphere; Schlenk technique;	72%

3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione (1000623-98-2) + tributyl(thien-2-yl)stannane (54663-78-4) → 3,6-di([2,2'-bithiophen]-5-yl)-2,5-bis(2-hexyldecyl)pyrrolo [3,4-c]pyrrole-1,4(2H,5H)-dione (1143585-34-5)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tris-(o-tolyl)phosphine In toluene at 90℃; for 24h; Stille Cross Coupling; Inert atmosphere;	72%

3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione (1000623-98-2) + 2-ethynylnaphthalene (2949-26-0) → 2,5-bis(2-hexyldecyl)-3,6-bis(5-(naphthalen-2-ylethynyl)thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); N-ethyl-N,N-diisopropylamine In toluene at 60℃; for 8h; Sonogashira Cross-Coupling; Inert atmosphere; Schlenk technique;	67%

tributyl(3-dodecylcyclopenta-1,3-dien-1-yl)stannane + 3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione (1000623-98-2) → C78H124N2O2S4 (1000623-99-3)

Conditions	Yield
tetrakis(triphenylphosphine) palladium(0) In toluene Heating / reflux;

3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione (1000623-98-2) + 2-(4-dodecylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1173788-58-3) → C62H97BrN2O2S3

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene at 115℃; for 24h; Suzuki coupling;	1.062 g

3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione (1000623-98-2) → 3,6-bis(5'-bromo-[2,2'-bithiophen]-5-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione (1143585-35-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: tris-(dibenzylideneacetone)dipalladium(0); tris-(o-tolyl)phosphine / toluene / 24 h / 90 °C / Inert atmosphere 2: N-Bromosuccinimide / chloroform / 6 h / 20 °C / Inert atmosphere; Darkness View Scheme

3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione (1000623-98-2) → 6,6'-([2,2'-bithiophene]-5,5'-diyl)bis(3-(5-bromothiophen-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione)

Conditions	Yield
With palladium diacetate; N-ethyl-N,N-diisopropylamine In toluene Inert atmosphere; Reflux;

3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione (1000623-98-2) + 2-([2,2'-bithiophen]-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (479719-88-5) → C54H75BrN2O2S4

Conditions

Yield

Stage #1: 3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione; 2-([2,2'-bithiophen]-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane With tris-(dibenzylideneacetone)dipalladium(0); tri tert-butylphosphoniumtetrafluoroborate In tetrahydrofuran for 0.5h; Suzuki Coupling; Inert atmosphere; Reflux; Stage #2: With potassium phosphate In tetrahydrofuran; water Suzuki Coupling; Inert atmosphere; Reflux;

3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione (1000623-98-2) + 4,4,5,5-tetramethyl-2-(12,22:25,32-terthiophen-15-yl)-1,3,2-dioxaborolane (849062-17-5) → C58H77BrN2O2S5

Conditions

Yield

Stage #1: 3,6-bis(5-bromo-2-thienyl)-2,5-dihydro-2,5-di(2'-hexyldecyl)-pyrrolo[3,4c]pyrrolo-1,4-dione; 4,4,5,5-tetramethyl-2-(12,22:25,32-terthiophen-15-yl)-1,3,2-dioxaborolane With tris-(dibenzylideneacetone)dipalladium(0); tri tert-butylphosphoniumtetrafluoroborate In tetrahydrofuran for 0.5h; Suzuki Coupling; Inert atmosphere; Reflux; Stage #2: With potassium phosphate In tetrahydrofuran; water Suzuki Coupling; Inert atmosphere; Reflux;

Upstream product

• 1044598-80-2 3,6-bis(5-bromothien-2-yl)-2,5-bis(2-hexyldecyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione 
• 2425-77-6 2-hexyldecan-1-ol 
• 1003-31-2 thiophene-2-carbonitrile 
• 1044598-79-9 7-(iodomethyl)pentadecane 

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